Complexation and sensing behavior of dansyl-appended cyclodextrins and cyclodextrin dimers with bile salts

Menno R. de Jong, Patrick Berthault, Arie van Hoek, Antonie J.W.G. Visser, Jurriaan Huskens, David N. Reinhoudt

Research output: Contribution to journalArticleAcademicpeer-review

10 Citations (Scopus)

Abstract

The dansyl-modified cyclodextrin derivatives 2 and 3 form complexes with the steroidal bile salts. The selectivity of the monomeric derivative 3 is similar to that of native β-cyclodextrin. All binding constants with 3 are lowered compared to β-cyclodextrin because of the competition for the cavity between the steroids and the dansyl moiety. Cholate ( 4a ) and deoxycholate ( 4b ) form weak complexes, the other bile salts ( 4c - e ) are complexed far more strongly. The difference is attributed to the absence of a 12-hydroxy group in the latter steroids. Data for dimer 2 reveal strongly enhanced binding of 4a and 4b and only slightly stronger complexes with the other steroids. Due to the low binding affinity of 3 for 4a and 4b , this receptor could not be used for their detection by fluorescence spectroscopy. Steroids 4c - e showed a decrease in fluorescence intensity. The detection of all steroids 4a - e was possible using 2 . The fluorescence intensity of the dimer increased or decreased, depending on which steroid was added.
Original languageEnglish
Pages (from-to)143-151
JournalSupramolecular chemistry
Volume14
Issue number2-3
DOIs
Publication statusPublished - 2002

Keywords

  • Cyclodextrin
  • Fluorescence
  • Dansyl group
  • Binding constants

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